Synthesis and Evaluation of a Photochromic Surfactant for Organic Reactions in Aqueous Media

Abstract

A novel photochromic azobenzene-based surfactant was described for organic chemistry in water. The molecule 4-butylazobenzyl-4'-triazologlucuronic acid sodium salt thus synthesized can be isomerized from its trans to its cis form reversibly in solution by simple light irradiation. That property allowed the recyclability of a model acetylation reaction performed in the surfactant media, compared to the well-known, commercially available sodium dodecyl sulfate surfactant media.

The Hydrophobic Effect Applied to Organic Synthesis: Recent Synthetic Chemistry “in Water”

“…[72] Len and co-workersh ave devisedaphoto-switchable surfactant that can be modulated by UV-light.T his new amphiphile, BABTGA,i ncludes am odified sugar as its hydrophilic portion, while bearing an azobenzene as its photochromic core within its hydrophobic subsection (Scheme 38). [73] This stimulus-responsivem oiety leads to reversible organization of the assemblies via trans-to-cis isomerization under UV irradiation (365 nm). Acetylation of numerousa romatic, and, to some degree, aliphatic amines,w as performed within the surfactant while in its trans form.…”

Improved Synthesis of 1-O-Acyl-β-d-Glucopyranose Tetraacetates

“…All solvents and reagents, except for compound 1 , were purchased from the commercial supplier Tansoole (Shanghai, China) and were used without further purification. Compound 1 was prepared according to the known method [ 26 ]. 4 Å MS were activated at 600 °C for one-day and kept in a dessicator.…”

Amphiphilic azobenzenes: Antibacterial activities and biophysical investigation of their interaction with bacterial membrane lipids

“…The emergence of nosocomial multi-drug resistant (MDR) bacterial strains is a growing concern in hospitals and underlines the urgent need for the development of novel antibacterial agents [1,2]. The azo compounds are used in a wide range of applications such as surfactants [3][4][5], catalysts [6], gelators [7], and liquid crystals [8,9]. Recently, azo-amphiphiles have been shown to exhibit a high biocide potential, especially if they contain a cationic head group such as quaternary ammonium salt.…”